(R)-tert-butyl 4-((5-((tert-butyldiphenylsilyl)oxy)hexyl)oxy)-4-(iodomethyl)piperidine-1-carboxylate → (R)-tert-butyl 4-((5-((tert-butyldiphenylsilyl)oxy)hexyl)oxy)-4-methylpiperidine-1-carboxylate

Participants

Reaction Steps

To a solution of (R)-tert-butyl 4-((5-((tert-butyldiphenylsilyl)oxy)hexyl)oxy)-4-(iodomethyl)piperidine-1-carboxylate (13 g, 19.12 mmol) in MeOH (100 mL) was added TEA (5.33 mL, 38.2 mmol) followed by 10% Pd—C (1.018 g, 0.956 mmol) and the resulting mixture was subjected to hydrogenolysis under PAR at 50 PSI. After 16 h, mixture was filtered through a pad of celite and the filtrate was concentrated. The residue was then purified by Biotage (0-15% EtOAc/hexane) to afford (R)-tert-butyl 4-((5-((tert-butyldiphenylsilyl)oxy)hexyl)oxy)-4-methylpiperidine-1-carboxylate (8.2 g, 14.81 mmol, 77% yield) as light yellow oil. 1H NMR (500 MHz, CDCl3) δ 7.73-7.67 (m, 4H), 7.48-7.35 (m, 6H), 3.86 (sxt, J=5.8 Hz, 1H), 3.72 (br. s., 2H), 3.24 (t, J=6.3 Hz, 2H), 3.10 (br. s., 2H), 1.78-1.66 (m, 3H), 1.59-1.51 (m, 1H), 1.50-1.47 (m, 6H), 1.47 (s, 9H), 1.14 (s, 3H), 1.10-1.03 (m, 12H). LCMS (M+Na)=576.7.

Provenance & Evidence